1,3,3-Trimethyl-2-methyleneindoline → HCID 49845114, compound

HRID 537635

Reaction equation

HRID 537635 reaction equation
[CH2:1]([N:3]([CH2:23][CH2:24][OH:25])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=[O:20])[C:12](=[N:21]O)[CH:11]=2)=[CH:6][CH:5]=1)[CH3:2].[CH3:26][N:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]([CH3:37])([CH3:36])[C:28]1=[CH2:38]>C(O)C>[CH2:1]([N:3]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]3[O:20][C:28]4([C:29]([CH3:37])([CH3:36])[C:30]5[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=5)[N:27]4[CH3:26])[CH:38]=[N:21][C:12]=3[CH:11]=2)=[CH:6][CH:5]=1)[CH2:23][CH2:24][OH:25])[CH3:2]

Participants

4

Reactant 2

HCID 83511,3,3-Trimethyl-2-methyleneindolineHCID 178464427HCID 178464427, compound

Product 1

HCID 49845114HCID 49845114, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 4-(4-(ethyl(2-hydroxyethyl)amino)phenyl)-2-(hydroxyimino)naphthalen-1(2H)-one (4.0 g, 11.89 mmol) in ethanol (100 ml) was treated with 1,3,3-trimethyl-2-methyleneindoline (2.68 g, 15.46 mmol) in one portion and heated to 100° C. in a sealed tube for 4 hrs. The mixture was then cooled to RT and left to stand overnight. The resulting suspension was evaporated in vacuo to approx 25 ml total volume, MeOH added (25 ml) and the mixture stored in the freezer for 3 hrs. After this time the product was collected by filtration and washed with a little methanol to give the product, 2-(ethyl(4-(1,3,3-trimethylspiro[indoline-2,2′-naphtho[1,2-b][1,4]oxazine]-6′yl)phenyl)amino)ethanol, as pale green fibres (4.15 g, 71%). Analysis of the product by 1H NMR gave a spectrum consistent with the structure.

Workup

  1. temperatureThe mixture was then cooled to RT
  2. waitleft
  3. customThe resulting suspension was evaporated in vacuo to approx 25 ml total volume, MeOH
  4. additionadded (25 ml)
  5. waitthe mixture stored in the freezer for 3 hrs
  6. filtrationAfter this time the product was collected by filtration
  7. washwashed with a little methanol

Sources & evidence

ORD record
ord-47a56ca07ce943e7ae9ac17951b04aec
Source dataset
uspto-grants-2014_10
Patent number
US08865029B2

Linked notes

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